Oakland Vacations from $359
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Wyndham Grand Pittsburgh Downtown
Downtown Pittsburgh
Price was $601, price is now $401 per person
$401
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Pittsburgh (PIT)
8.2/10 Very Good! (3,030 reviews)
Overall we like this hotel, clean, great location, super helpful staff. On a recent stay our room had a bit of an odor, just enough to notice when you walked into the room. And the mini-fridge, which is usually in a cabinet as I recall, was just sitting on the floor by itself. This room just seemed a little...off. For a quick one-night stay it wasn't worth it to us to ask to change rooms, and it wouldn't stop us from staying there again.
Reviewed on Oct 10, 2025
DoubleTree by Hilton Pittsburgh Airport
Save 100% on your flight
Price was $745, price is now $522 per person
$522
per person
Dec 24 - Dec 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Pittsburgh (PIT)
8.6/10 Excellent! (1,004 reviews)
Parking area was safe & well lit. Nice room. Would be nice to have a night light in the bathroom.
Reviewed on Oct 10, 2025
Omni William Penn Hotel
Downtown Pittsburgh
Save 100% on your flight
Price was $860, price is now $612 per person
$612
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Pittsburgh (PIT)
9/10 Wonderful! (1,671 reviews)
We were very happy with our stay, room was large, elevators quick. Easy access to everything
Reviewed on Oct 8, 2025
Fairmont Pittsburgh
Downtown Pittsburgh
Save 100% on your flight
Price was $882, price is now $640 per person
$640
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Pittsburgh (PIT)
8.8/10 Excellent! (1,003 reviews)
The staffs are friendly and the rooms clean and comfortable. Highly recommend it!
Reviewed on Oct 6, 2025
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $158 total per night from Oct 19 to Oct 20
$158 total
Oct 19 - Oct 20
Total with taxes and fees
8.8/10 Excellent! (460 reviews)
"Great stay. Thank you!"
Reviewed on Sep 30, 2025
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive, Pittsburgh, PA
Fully refundable
$112 nightly
The price is $127 total per night from Nov 3 to Nov 4
$127 total
Nov 3 - Nov 4
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"The room is very up-to-date and very comfortable. There is plenty of space, too."
Reviewed on Oct 6, 2025
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard, Pittsburgh, PA
Fully refundableReserve now, pay when you stay
$212 nightly
The price is $242 total per night from Nov 9 to Nov 10
$242 total
Nov 9 - Nov 10
Total with taxes and fees
9/10 Wonderful! (691 reviews)
"10/10"
Reviewed on Sep 29, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Ghosts Steel City Haunted Tour
$32
per adult
100% of travellers recommend
Pittsburgh: Golden Triangle Guided Walking Tour at Sunset
$28
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
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- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
- Pittsburgh Vacations
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- Clemente Museum
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- Contemporary Craft
- Market Square
- Visit Pittsburgh
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- PPG Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.